KR101837974B1 - 8-하이드록시-퀴놀린 유도체 - Google Patents
8-하이드록시-퀴놀린 유도체 Download PDFInfo
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- KR101837974B1 KR101837974B1 KR1020127030702A KR20127030702A KR101837974B1 KR 101837974 B1 KR101837974 B1 KR 101837974B1 KR 1020127030702 A KR1020127030702 A KR 1020127030702A KR 20127030702 A KR20127030702 A KR 20127030702A KR 101837974 B1 KR101837974 B1 KR 101837974B1
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- KR
- South Korea
- Prior art keywords
- group
- methyl
- compound
- quinolin
- trifluoromethyl
- Prior art date
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- C—CHEMISTRY; METALLURGY
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- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/24—Oxygen atoms attached in position 8
- C07D215/26—Alcohols; Ethers thereof
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Cardiology (AREA)
- Toxicology (AREA)
- Psychology (AREA)
- Biochemistry (AREA)
- Hospice & Palliative Care (AREA)
- Vascular Medicine (AREA)
- Pain & Pain Management (AREA)
- Pulmonology (AREA)
- Dermatology (AREA)
- Gastroenterology & Hepatology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
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HUP1000243 | 2010-05-06 | ||
HU1000243A HUP1000243A2 (en) | 2010-05-06 | 2010-05-06 | 8-hidroxy-quinoline derivatives |
PCT/HU2011/000043 WO2011148208A1 (en) | 2010-05-06 | 2011-05-06 | 8-hydroxy-quinoline derivatives |
Publications (2)
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KR20130029772A KR20130029772A (ko) | 2013-03-25 |
KR101837974B1 true KR101837974B1 (ko) | 2018-03-13 |
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KR1020127030702A KR101837974B1 (ko) | 2010-05-06 | 2011-05-06 | 8-하이드록시-퀴놀린 유도체 |
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CN (1) | CN102985407B (hu) |
AU (1) | AU2011256989B2 (hu) |
CA (1) | CA2798419C (hu) |
CY (1) | CY1122426T1 (hu) |
DK (1) | DK2566849T3 (hu) |
EA (1) | EA021026B1 (hu) |
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RS (1) | RS59678B1 (hu) |
SI (1) | SI2566849T1 (hu) |
WO (1) | WO2011148208A1 (hu) |
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HUP1500098A2 (hu) | 2015-03-09 | 2016-09-28 | Avidin Kft | 8-hidroxikinolin származékok új enantiomerjei és szintézisük |
EP3361871A4 (en) * | 2015-10-12 | 2019-06-26 | Health Research, Inc. | METHODS FOR INDUCING APOPTOSIS IN CANCER CELLS |
CN105367553A (zh) * | 2015-12-04 | 2016-03-02 | 广东工业大学 | 一种他克林-8-羟(胺)基喹啉衍生物及其应用 |
HUP1600234A2 (en) | 2016-04-05 | 2017-12-28 | Mta Termeszettudomanyi Kutatokoezpont | Mdr-reversing 8-hydroxy-quinoline derivatives |
WO2024073624A2 (en) * | 2022-09-28 | 2024-04-04 | The Research Foundation For The State University Of New York | Antiproliferative betti bases and prodrugs thereof |
Citations (1)
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WO2009151972A1 (en) * | 2008-05-28 | 2009-12-17 | , The United States Of America, As Represented By The Secretary Of The Army, On Behalf Of U.S. Army Medical Research And Materiel Command | Small molecule inhibitors of botulinum neurotoxins |
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WO1999015179A1 (en) | 1997-09-25 | 1999-04-01 | Regents Of The University Of Minnesota | Methods of limiting apoptosis of cells |
US6184210B1 (en) | 1997-10-10 | 2001-02-06 | Cytovia, Inc. | Dipeptide apoptosis inhibitors and the use thereof |
CA2319131A1 (en) | 1998-01-26 | 1999-07-29 | Walter H. Moos | Mitochondria protecting agents for treating mitochondria associated diseases |
US6737511B1 (en) | 1999-08-16 | 2004-05-18 | The United States Of America As Represented By The Department Of Health And Human Services | Receptor-mediated uptake of an extracellular BCL-xL fusion protein inhibits apoptosis |
EP1212295B1 (en) | 1999-08-27 | 2008-10-01 | Cytovia, Inc. | Substituted alpha-hydroxy acid caspase inhibitors and the use thereof |
US6890896B1 (en) | 1999-11-18 | 2005-05-10 | Ceremedix, Inc. | Compositions and methods for counteracting effects of reactive oxygen species and free radicals |
US6531464B1 (en) | 1999-12-07 | 2003-03-11 | Inotek Pharmaceutical Corporation | Methods for the treatment of neurodegenerative disorders using substituted phenanthridinone derivatives |
US6476048B1 (en) | 1999-12-07 | 2002-11-05 | Inotek Pharamaceuticals Corporation | Substituted phenanthridinones and methods of use thereof |
US6534651B2 (en) | 2000-04-06 | 2003-03-18 | Inotek Pharmaceuticals Corp. | 7-Substituted isoindolinone inhibitors of inflammation and reperfusion injury and methods of use thereof |
GB0011095D0 (en) | 2000-05-08 | 2000-06-28 | Black James Foundation | astrin and cholecystokinin receptor ligands (III) |
AU2002213174A1 (en) | 2000-10-13 | 2002-04-22 | Massaharu Akao | Treatment of apoptotic cell death |
WO2002048092A2 (en) | 2000-12-15 | 2002-06-20 | Mitokor | Compounds for altering mitochondrial function and cellular responses |
US7601846B2 (en) | 2001-06-26 | 2009-10-13 | The Regents Of The University Of California | Compounds having activity as inhibitors of apoptosis |
EP1414948B1 (en) | 2001-07-10 | 2009-09-16 | Biogen Idec Inc. | Inhibition of apoptosis process and improvement of cell performance |
DE10144153A1 (de) | 2001-09-07 | 2003-03-27 | Newfrey Llc | Halteclip mit versetzten Rastfingern |
AU2003211102B2 (en) | 2002-02-13 | 2010-03-04 | Beth Israel Deaconess Medical Center, Inc. | Methods of treating vascular disease |
EP1603567A4 (en) | 2003-02-28 | 2006-10-18 | Inotek Pharmaceuticals Corp | TETRACYCLIC BENZAMIDE DERIVATIVES AND METHOD OF USE THEREOF |
US7449464B2 (en) | 2003-03-12 | 2008-11-11 | Kudos Pharmaceuticals Limited | Phthalazinone derivatives |
WO2004105700A2 (en) | 2003-05-28 | 2004-12-09 | Guildford Pharmaceuticals, Inc. | Compounds, methods and pharmaceutical compositions for inhibiting parp |
RU2376028C2 (ru) | 2004-01-23 | 2009-12-20 | Корнелл Рисеч Фаундейшн, Инк. | Способ уменьшения окислительного повреждения (варианты) |
TWI375673B (en) | 2005-04-11 | 2012-11-01 | Abbott Lab | 1h-benzimidazole-4-carboxamides substituted with a quaternary carbon at the 2-position are potent parp inhibitors |
ATE461923T1 (de) | 2005-11-15 | 2010-04-15 | Abbott Lab | Substituierte 1h-benzimidazol-4-carbonsäureamide sind wirksame parp-inhibitoren |
US7528174B2 (en) | 2006-01-06 | 2009-05-05 | University Of Pittsburgh-Of The Commonwealth System Of Higher Education | Selective targeting agents for mitochondria |
CA2658793A1 (en) * | 2006-07-25 | 2008-02-07 | Daniel Dumas | Quinoline derivatives |
EP2139460A4 (en) * | 2007-03-20 | 2011-09-07 | Univ Brandeis | COMPOSITIONS AND METHODS FOR THE DIAGNOSIS, TREATMENT AND PREVENTION OF AMYOTROPHER LATERAL SCLEROSIS AND ASSOCIATED NEUROLOGICAL DISEASES |
US8183236B2 (en) * | 2007-04-12 | 2012-05-22 | University Of Southern California | Compounds with HIV-1 integrase inhibitory activity and use thereof as anti-HIV/AIDS therapeutics |
EP2148944A1 (en) | 2007-05-25 | 2010-02-03 | Burnham Institute for Medical Research | Inhibitors of thapsigargin-induced cell death |
US8138356B2 (en) * | 2007-10-16 | 2012-03-20 | Angiogeney, Inc. | Chemical inhibitors of inhibitors of differentiation |
EP2521553A4 (en) * | 2010-01-06 | 2013-08-28 | Errico Joseph P | METHODS AND COMPOSITIONS FOR THE DEVELOPMENT OF TARGETED MEDICAMENTS |
US8658170B2 (en) * | 2010-01-06 | 2014-02-25 | Joseph P. Errico | Combination therapy with MDM2 and EFGR inhibitors |
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Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2009151972A1 (en) * | 2008-05-28 | 2009-12-17 | , The United States Of America, As Represented By The Secretary Of The Army, On Behalf Of U.S. Army Medical Research And Materiel Command | Small molecule inhibitors of botulinum neurotoxins |
Non-Patent Citations (4)
Title |
---|
Journal f. prakt. Chemie., Vol. 327, No. 5, pp.871-877 (1985)* |
Journal of Organic Chemistry, Vol. 19, No. 6, pp.907-909 (1954)* |
Journal of the American Chemistry Society, Vol. 75, No. 17, pp. 4306-4307 (1953)* |
Molecular and Cellular Endocronology, Vol. 301, pp. 245-250 (2009)* |
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CA2798419C (en) | 2021-01-05 |
CY1122426T1 (el) | 2021-01-27 |
KR20130029772A (ko) | 2013-03-25 |
HRP20192278T1 (hr) | 2020-03-06 |
CN102985407A (zh) | 2013-03-20 |
EA021026B1 (ru) | 2015-03-31 |
EA201270787A1 (ru) | 2013-04-30 |
US8871937B2 (en) | 2014-10-28 |
CA2798419A1 (en) | 2011-12-01 |
US20130131096A1 (en) | 2013-05-23 |
HU1000243D0 (en) | 2010-06-28 |
CN102985407B (zh) | 2015-09-09 |
ES2761832T3 (es) | 2020-05-21 |
MX337999B (es) | 2016-03-30 |
RS59678B1 (sr) | 2020-01-31 |
PT2566849T (pt) | 2020-01-06 |
HUE050886T2 (hu) | 2021-01-28 |
NZ603967A (en) | 2014-06-27 |
MX2012012883A (es) | 2013-03-20 |
SI2566849T1 (sl) | 2020-02-28 |
EP2566849A1 (en) | 2013-03-13 |
AU2011256989B2 (en) | 2014-08-21 |
JP5812541B2 (ja) | 2015-11-17 |
PL2566849T3 (pl) | 2020-03-31 |
EP2566849B1 (en) | 2019-09-18 |
AU2011256989A1 (en) | 2013-01-10 |
DK2566849T3 (da) | 2020-01-02 |
HUP1000243A2 (en) | 2012-01-30 |
WO2011148208A1 (en) | 2011-12-01 |
JP2013525473A (ja) | 2013-06-20 |
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